Bioactive and other sesquiterpenes from Chiloscyphus rivularis.
Bioassay-directed fractionation of the methyl ethyl ketone extract of Chiloscyphus rivularis yielded five new sesquiterpenes, 12-hydroxychiloscyphone (2), chiloscypha-2,7-dione (3), 12-hydroxychiloscypha-2,7-dione (4), chiloscypha-2,7,9-trione (5), and rivulalactone (6) in addition to the known sesquiterpenes, 4-hydroxyoppositan-7-one (7), chiloscyphone (1), and isointermedeol (8). The structure and stereochemistry of rivulalactone, a novel trinorsesquiterpene, was confirmed by its synthesis starting from 1. Compound 2 showed selective bioactivity in our yeast-based DNA-damaging assay and cytotoxicity to human lung carcinoma cells.
Wu
C
C
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg 24061, USA.
Gunatilaka
A A
AA
McCabe
F L
FL
Johnson
R K
RK
Spjut
R W
RW
Kingston
D G
DG
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D004249:DNA Damage; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000302:isolation & purification* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D012717:Sesquiterpenes; C528862:isointermedeol